WO1993007751A1 - Fongicides servant a lutter contre le pietin-echaudage des cereales - Google Patents

Fongicides servant a lutter contre le pietin-echaudage des cereales Download PDF

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Publication number
WO1993007751A1
WO1993007751A1 PCT/US1992/008633 US9208633W WO9307751A1 WO 1993007751 A1 WO1993007751 A1 WO 1993007751A1 US 9208633 W US9208633 W US 9208633W WO 9307751 A1 WO9307751 A1 WO 9307751A1
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Prior art keywords
compound
alkyl
halo
methyl
haloalkyl
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PCT/US1992/008633
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English (en)
Inventor
Diane Susan Braccolino
Matthew James Graneto
Dennis Paul Phillion
Wendell Gary Phillips
Karey Alan Van Sant
Daniel Mark Walker
Sai Chi Wong
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Monsanto Company
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Application filed by Monsanto Company filed Critical Monsanto Company
Priority to SK448-94A priority Critical patent/SK44894A3/sk
Priority to AU28093/92A priority patent/AU664392B2/en
Priority to HU9401110A priority patent/HU219131B/hu
Priority to CA002119155A priority patent/CA2119155C/fr
Priority to PL92303097A priority patent/PL170837B1/pl
Priority to CZ1994887A priority patent/CZ290470B6/cs
Publication of WO1993007751A1 publication Critical patent/WO1993007751A1/fr

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    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
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    • C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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    • C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/69—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
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    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
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    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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Definitions

  • This invention relates to a method for the control of Take-All disease in plants, particularly cereals, by the use of certain substituted aryl
  • Gaeumannomyces species also infect other cereal crops, for example, rice and oats; and turf.
  • the present invention provides a method of controlling disease caused by Gaeumannomyces species in plants comprising applying to the plant locus, that is, the plant itself, its seed, or the soil, a fungicidally effective amount of a fungicide of the formula
  • Z 1 and Z 2 are C or N and are part of an aromatic ring selected from benzene, pyridine, thiophene, furan, pyrrole, pyrazole, thiazole, and
  • B is -W m -Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl,
  • Q is C, Si, Ge, or Sn
  • W is -C(R 3 ) p H (2-p) -; or when Q is C, w is selected from
  • n 0, 1, 2 , or 3;
  • n 0 or 1
  • p 0, 1, or 2;
  • each R is independently selected from
  • alkoxycarbonyl (alkylthio)carbonyl
  • alkylaminocarbonyl dialkylaminocarbonyl, alkylsulfinyl, or alkylsulfonyl;
  • cycloalkyloxy cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio) carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo;
  • each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino;
  • R 3 is C1-C4 alkyl
  • R 4 is C1-C4 alkyl, haloalkyl, alkoxy, alkylthio,
  • alkylamino or dialkylamino
  • R 7 is C1-C4 alkyl, haloalkyl, or phenyl, optionally
  • amine in -C(X)-amine means an
  • substituents for the amino radical include, but are not limited to, hydroxy; alkyl, alkenyl, and alkynyl, which may be straight or branched chain or cyclic; alkoxyalkyl; haloalkyl; hydroxyalkyl; alkylthio; alkylthioalkyl; alkylcarbonyl; alkoxycarbonyl;
  • nitrogen-bearing heterocycles which are bonded at a nitrogen to -C(X)-, include, but are not limited to, morpholine, piperazine, piperidine, pyrrole, pyrrolidine, imidazole, and triazoles, each of which may be optionally substituted with one or more C1-C6 alkyl groups.
  • amino radicals useful in the present invention include, but are not limited to, ethylamino, methylamino, propylamino, 2-methylethylamino, 1-propenylamino, 2-propenylamino, 2-methyl-2- propenylamino, 2-propynylamino, butylamino,
  • nitrophenylamino 1-phenylethylamino, N-(methyl)-3-phenyl-2-propenylamino, benzotriazolylphenylmethyl, 2-pyridinylmethylamino, N-(ethyl)-2-pyridinylmethylamino, 2-thienylmethylamino, and furylmethylamino.
  • amino radicals include methylhydrazino, dimethylhydrazino, N-ethylanilino, and
  • the amine may also be substituted with diethyl N-ethylphosphoramidic acid, t-butoxycarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, etc.
  • diethyl N-ethylphosphoramidic acid diethyl N-ethylphosphoramidic acid
  • t-butoxycarbonyl methoxycarbonyl
  • ethoxycarbonyl propoxycarbonyl
  • ethylamino is preferred.
  • Examples of B include, but are not limited to, trimethylsilyl, ethyldimethylsilyl, diethylmethylsilyl, triethylsilyl, dimethylpropyIsilyl, dipropylmethylsilyl, dimethyl-1-(methyl)ethylsilyl, tripropylsilyl,
  • trimethylsilyl is preferred.
  • B examples include 1,1-dimethylethyl, 1,1-dimethylpropyl, 1,1-dimethylbutyl, 1,1-dimethylpentyl, 1-ethyl-1-methylbutyl, 2,2- dimethylpropyl, 2,2-dimethylbutyl, 1-methyl-1- ethylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2-trimethyIbutyl, 1,1,2,2-tetramethylpropyl, 1,1- dimethyl-2-propenyl, 1,1,2-trimethyl-2-propenyl, 1,1- dimethyl-2-butenyl, 1,1-dimethyl-2-propynyl, 1,1- dimethyl-2-butynyl, 1-cyclopropyl-1-methylethyl, 1- cyclobutyl-1-methylethyl, 1-cyclopentyl-1-methylethyl, 1-(1-cyclopentenyl)-1-methylethyl
  • B are 1,1-dimethylethylamino, 1,1-dimethylpropylamino, 1,1-dimethylbutylamino, 1,1- dimethylpentylamino, 1-ethyl-1-methylbutylamino, 2,2-dimethylpropylamino, 2,2-dimethylbutylamino, 1-methyl-1-ethylpropylamino, 1,1-diethylpropylamino, 1,1,2-trimethylpropylamino, 1,1,2-trimethylbutylamino,
  • 1,1,2,2-tetramethylpropylamino 1,1-dimethyl-2-propenylamino, 1,1,2-trimethyl-2-propenylamino, 1,1-dimethyl-2-butenylamino, 1,1-dimethyl-2-propynylamino, 1,1-dimethyl-2-butynylamino, 1-cyclopropyl-1-methylethylamino, 1-cyclobutyl-1-methylethylamino, 1-cyclopentyl-1-methylethylamino, 1-(1-cyclopentenyl)-1-methylethylamino, 1-cyclohexyl-1-methylethylamino, 1-(1-cyclohexenyl)-1-methylethylamino, 1-methyl-1-phenylethylamino, 1,1-dimethyl-2-chloroethylamino, 1,1-dimethyl-3-chloropropylamino, 1,1-dimethyl-2-meth
  • any of these groups may also have a methyl substitution on the nitrogen, as in N-(methyl)-1,1-dimethylethylamino and N- (methyl)-1,1-dimethylpropylamino.
  • N-(methyl)-1,1-dimethylethylamino and N- (methyl)-1,1-dimethylpropylamino are preferred.
  • B include 1,1-dimethylethoxy, 1,1-dimethylpropoxy, 1,1-dimethylbutoxy, 1,1-dimethylpentoxy, 1-ethyl-1-methylbutoxy, 2,2-dimethylpropoxy, 2,2-dimethylbutoxy, 1-methyl-1-ethylpropoxy, 1,1-diethylpropoxy, 1,1,2-trimethylpropoxy, 1,1,2-trimethylbutoxy, 1,1,2,2-tetramethylpropoxy, 1,1-dimethyl-2-propenoxy, 1,1,2-trimethyl-2-propenoxy, 1,1-dimethyl-2-butenoxy, 1,1-dimethyl-2-propynyloxy, 1,1-dimethyl-2-butynyloxy, 1-cyclopropyl-1-methylethoxy, 1-cyclobutyl-1-methylethoxy, 1-cyclopentyl-1-methylethoxy , 1- ( 1-cyclopentenyl)-1-methylethoxy, 1-cyclohexyl-1-methylethoxy, 1-(
  • B examples include 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 1-methyleyelopropylamino, l1methylcyclobutylamino, 1-methylcyclopentylamino, 1-methyl- cyclohexylamino, N-(methyl)-1-methylcyclopropylammo, N-(methyl)-1-methyleyelobutylamino, N-(methyl)-1-methylcyclopentylamino, and N-(methyl)-1-methylcyclohexylamino.
  • R n may be any substituent(s) which do(es) not unduly reduce the effectiveness of the compounds to function in the method of disease control.
  • R n is generally a small group; "n" is preferably 1 for benzene rings and 2 for furan and thiophene. R is more
  • n is not zero when B is trimethylsilyl and A is N,N-diethylaminocarbonyl, N,N- bis(1-methylethyl)aminocarbonyl, N-methylaminothiocarbonyl, N-ethylaminocarbonyl, 1-piperidinylcarbonyl, or N-phenylaminocarbonyl; or when B is orthotolyl and A is N,N-diethylaminocarbonyl, N,N-bis(1- methylethyl)aminocarbonyl, N-methylaminocarbonyl, or O-methylcarbamyl; or when B is 1,1-dimethylethyl and A is N,N-dimethylaminothiocarbon
  • the invention also provides fungicidal
  • compositions useful in said method are compositions useful in said method.
  • alkyl radical straight or branched chain, having, unless otherwise indicated, from 1 to 10 carbon atoms.
  • alkenyl and alkynyl mean unsaturated radicals having from 2 to 7 carbon atoms.
  • alkenyl groups include ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1-methylethenyl, and the like.
  • alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1,1-dimethyl-2-propynyl, and so forth.
  • Substituent groups may also be both alkenyl and alkynyl, for example, 6,6-dimethyl-2-hepten-4-ynyl.
  • alkoxy means an alkyl group having, unless otherwise indicated, from 1 to 10 carbon atoms connected via an ether linkage. Examples of such alkoxy groups include methoxy, ethoxy, propoxy, 1-methylethoxy, and so forth.
  • alkoxyalkyl means an ether radical having, unless otherwise indicated, from 1 to 10 carbon atoms. Examples of such alkoxyalkyl groups include methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, and so forth.
  • dialkylamino and “dialkylamino” each mean an amino group having, respectively, 1 or 2 hydrogens replaced with an alkyl group.
  • haloalkyl means an alkyl radical having one or more hydrogen atoms replaced by halogens, including radicals having all hydrogen atoms substituted by halogen. Examples of such
  • haloalkyl groups are fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, trichloromethyl, and so forth.
  • halo means a radical selected from chloro, bromo, fluoro, and iodo.
  • Control of Gg diseases, including Take-All, using a chemical control agent may be accomplished in several ways.
  • the agent may be applied directly to soil
  • compositions of the present invention are comprised of a fungicidally effective amount of one or more of the compounds described above and one or more adjuvants.
  • the active ingredient may be present in such compositions at levels from 0.01 to 95 percent by weight.
  • Other fungicides may also be included to provide a broader spectrum of fungal control. The choice of fungicides will depend on the crop and the diseases known to be a threat to that crop in the location of interest.
  • the fungicidal compositions of this invention may contain at least one active ingredient and an adjuvant in liquid or solid form.
  • compositions are prepared by admixing the active ingredient with an adjuvant including diluents, extenders, carriers, and conditioning agents to provide compositions in the form of finely-divided particulate solids, granules, pellets, solutions, dispersions or emulsions.
  • an adjuvant such as a finely-divided solid, a liquid of organic origin, water, a wetting agent, a dispersing agent, an emulsifying agent or any suitable combination of these.
  • Suitable wetting agents are believed to include alkyl benzene and alkyl naphthalene sulfonates, sulfated fatty alcohols, amines or acid amides, long chain acid esters of sodium isothionate, esters of sodium
  • sulfosuccinate sulfated or sulfonated fatty acid esters, petroleum sulfonates, sulfonated vegetable oils, ditertiary acetylenic glycols, polyoxyethylene derivatives of alkylphenols (particularly isooctylphenol and nonylphenol) and polyoxyethylene derivatives of the mono-higher fatty acid esters of hexitol anhydrides (e.g., sorbitan).
  • Preferred dispersants are methyl, cellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkyl naphthalene sulfonates, sodium
  • Stabilizers may also be used to produce stable emulsions, such as magnesium aluminum silicate and xanthan gum.
  • compositions include dust concentrates comprising from 0.1 to 60% by weight of the active ingredient on a suitable extender, optionally including other adjuvants to improve handling properties, e.g., graphite. These dusts may be diluted for application at concentrations within the range of from about 0.1-10% by weight.
  • Concentrates may also be aqueous emulsions, prepared by stirring a nonaqueous solution of a water-insoluble active ingredient and an emulsification agent with water until uniform and then homogenizing to give stable emulsion of very finely-divided particles.
  • they may be aqueous suspensions, prepared by milling a mixture of a water-insoluble active ingredient and wetting agents to give a suspension, characterized by its extremely small particle size, so that when diluted, coverage is very uniform. Suitable concentrations of these formulations contain from about 0.1-60% preferably 5-50% by weight of active ingredient.
  • ingredients of this invention for use in seed treatment include propylene glycol, furfuryl alcohol, other alcohols or glycols, and other solvents which do not substantially interfere with seed germination. If the active ingredient is to be applied to the soil, then solvents such as N,N-dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, hydrocarbons, and water-immiscible ethers, esters, or ketones.
  • the concentrate compositions herein generally contain from about 1.0 to 95 parts (preferably 5-60 parts) active ingredient, about 0.25 to 50 parts
  • Granules are physically stable particulate compositions
  • a surface active agent such as those listed hereinbefore, or for example, propylene glycol, can be present in the
  • Natural clays, pyrophyllites, illite, and vermiculite are examples of operable classes of
  • the preferred extenders are the porous, absorptive, preformed particles such as preformed and screened particulate attapulgite or heat expanded, particulate vermiculite and the finely-divided clays such as kaolin clays, hydrated attapulgite or bentonitic clays. These extenders are sprayed or blended with the active ingredient to form the
  • the granular compositions of this invention may contain from about 0.1 to about 30 parts by weight of active ingredient per 100 parts by weight of clay and 0 to about 5 parts by weight of surface active agent per 100 parts by weight of particulate clay.
  • the method of the present invention may be carried out by mixing the composition comprising the active ingredient into the seed prior to planting at rates from 0.01 to 50 g per kg of seed, preferably from 0.1 to 5 g per kg, and more preferably from 0.2 to 2 g per kg. If application to the soil is desired, the compounds may be applied at rates from 10 to 1000 g per hectare, preferably from 50 to 500 g per hectare. The higher application rates will be needed for situations of light soils or greater rainfall or both.
  • the compounds useful in the present invention may be prepared by methods known to those of ordinary skill in the art.
  • the following examples illustrate some of these methods and are illustrative only; they are not meant to be limiting in any way.
  • Method B Ortho-introduction of Electrophiles into N,N-dialkylbenzamides via Inverse Addition.
  • Example f The compound of Example f (5.0 g, 27.2 mmol), TMEDA (6.6 g, 57.1 mmol), and THF (100 Ml) were stirred at -78 °C under nitrogen, and 1.3M s-BuLi in cyclohexane (44 mL, 57.1 mmol) was added dropwise. The mixture was stirred for 15 min and trimethylborate (3.1 g, 29.9 mmol) was added all at once. The mixture was then stirred at -78 °C for 30 min before warming to RT. It was then poured into 10% HCl (100 mL). This mixture was made basic with sat aq NaHCO 3 and extracted with ether.
  • This compound (1.05 eq) in ethanol (2 mL) is added to an appropriate aryl, benzyl, or vinyl bromide (1 eq) and catalytic tetrakis(triphenylphosphine)- palladium(O) in toluene (20 mL) at RT under nitrogen.
  • Sodium carbonate (4 mL of a 2M aq solution) was then added and the resulting mixture was heated to reflux (4- 24 h) and monitored by TLC.
  • the mixture was then cooled to room temperature, diluted with additional toluene (20 mL), filtered through celite/silica, washed with water, dried (MgSO 4 ), and concentrated. If needed, the crude product was purified by chromatography or recrystallization from ethyl acetate/hexanes.
  • Example c 2-Bromo-6-(trimethylsilyl)benzoic acid.
  • the mixture was extracted with two 100 mL portions of ether, which were combined and washed three times with sat aq NaHCO 3 solution.
  • the bicarbonate solution was acidified with 25% citric acid and extracted with three 100 mL portions of ether. These extracts were combined, dried (MgSO4), and concentrated.
  • the crude product was purified by recrystallization from ether/hexanes, and the desired product was recovered as a white solid in 35% yield. m.p. 139-141 °C.
  • Example c The title compound was prepared from the compound of Example c according to the procedure of Example b.
  • 2,6-Difluorobenzoyl chloride 100 g, 566 mmol was added dropwise over 2 h to a vigorously stirred and ice water cooled mixture of 2-bromoethyl amine hydrobromide (116.05 g, 566 mmol), benzyltriethylammonium chloride (5 g, 22.0 mmol), 10% aq NaOH (680 mL, 1.7 mol), and CH 2 Cl 2 (1.5 L).
  • Example k N-ethyl t-butyImethyleneimine.
  • N-methyl-N-[2-(2-tert-butylphenylcarboxy)-1,1- dimethylethyl]trifluoromethanesulfonamide (1 eq) was saponified in a 2.0M solution of KOH (3 eq) in DMSO at 110 °C for 4 h. The resulting solution was cooled, diluted with water, and extracted twice with ether.
  • N,N-diethyl-2-tert-butylbenzamide (1.00 g, 4.3 mmol) was used in General Method A to afford 1.05 g of the title compound as a yellow oil, a 99% yield.
  • Example 9 (0.6 g, 2 mmol), dissolved in a minimum amount of THF. After stirring for 10 min, Mel (0.98 g, 6.9 mmol) was injected. The mixture was stirred for 1 h; 15 mL of 25% citric acid was added and the mixture
  • Example 5 (10.45 g, 37 mmol), dissolved in a minimum amount of THF. After stirring for 10 min, Mel (15.8 g, 0.1114 mol) was injected. The mixture was stirred for 1 h and 25% citric acid (15 mL) was added. The mixture was extracted three times with ether; the ether extracts were combined and washed twice with water, dried
  • N-ethyl-3-fluorobenzamide (4.18 g, 0.025 mol) (prepared from 3-fluorobenzoic acid using the procedures of Examples b, and f), dissolved in a minimum amount of THF, was used in General Method C and purified by HPLC, eluting with 3:7 ethyl acetate/hexanes. The title compound was recovered as a white solid in 53% yield, m.p. 80-82 °C.
  • Example 13 The compound of Example 13 was reacted with MeI using General Method A to prepare the title compound.
  • the following compounds were prepared using General Method A or B.
  • the starting materials are N,N-diethyl-3-fluorobenzamide, which is prepared from 3-fluorobenzoic acid as generally described above, and an appropriate electrophile.
  • reaction was diluted with ethyl acetate and extracted with dilute aq HCl, then with sat aq
  • Example 46 The compound of Example f (2.2 g, 0.012 mol) was reacted with TMSCl (3.91 g, 0.036 mol) using General Method A. The title compound was recrystallized from ether/hexanes as a solid, m.p. 105-107 °C.
  • Example 46
  • N-Ethylbenzamide (74.5 g, 500 mmol) and TMSCl (135.8 g, 1.25 mol) were combined according to General Method C and purified by HPLC with 1:4 ethyl
  • the title compound was prepared from the compound of Example 1 and Lawesson's reagent according to the procedure for Example 51.
  • the crude product was flash chromatographed on a 6" silica gel column with 1:19 ethyl acetate/hexanes and then recrystallized from hexanes to give 820 mg of the title compound as a white solid, a 78% yield. m.p. 68-69 °C.
  • Example 41 The compound of Example 41 (1.2 g, 4.1 mmol) and sodium borohydride (200 mg, 5.3 mmol) in ethanol (20 mL) were stirred at ambient temperature for 2 h. The solution was concentrated and partitioned between ether and 10% citric acid. The ether layer was washed with water and then brine, dried (MgSO 4 ), concentrated, and recrystallized from cold hexanes to afford 1.0 g of the title compound, an 82% yield, m.p. 107-108 °C.
  • the title compound was prepared from this compound and 2.0 eq TMSCl according to General Method A.
  • the crude product was purified by HPLC with 1:9 ethyl acetate/hexanes to give 4.8 g of the desired product as a clear oil, an 84% yield.
  • N,N-Diethyl-4-methylbenzamide was prepared from 4-methylbenzoyl chloride and diethylamine according to General Method E1.
  • the crude product was recrystallized from cold hexanes to give 30.4 g of the desired compound as a white solid, a 98% yield, m.p. 54 °C.
  • the title compound was prepared from this compound and 3.0 eq TMSCl according to General Method A.
  • the crude product was purified by HPLC with 3:17 ethyl acetate/hexanes to give 7.0 g of the title compound as a clear oil, an 89% yield.
  • the title compound was prepared from the compound of Example 58 and 1.2 eq hexachloroethane according to General Method A. Purification by HPLC with 1:9 ethyl acetate/hexanes afforded 1.6 g of the title compound as a clear oil, a 54% yield.
  • N,N-Diethyl-2-(trifluoromethyl)benzamide was prepared from 2-trifluoromethylbenzoyl chloride and diethylamine according to General Method E1.
  • the title compound was prepared from this compound and 3.0 eq TMSCl according to General Method A.
  • the crude material was purified by HPLC with 3:17 ethyl acetate/hexanes to afford 2.7 g of the title compound as a clear oil, an 85% yield.
  • N,N-Diethyl-2,5-bis(trifluoromethyl)benzamide was prepared from 2, 5-bis (trifluoromethyl) benzoyl chloride and diethylamine according to General Method E1.
  • the desired intermediate was isolated in quantitative yield (11.3 g) without additional purification.
  • the title compound was prepared from this compound and 3.7 eq TMSCl according to General Method A. Purification by HPLC with 1:19 ethyl acetate/hexanes, followed by kugelrohr distillation (90 @ 0.1 mm Hg) afforded 2.0 g of the title compound as a white solid, a 52% yield, m.p. 55-56 °C.
  • Compound 64 N,N-diethyl-3-methyl-2-(trimethylsilyl)-benzamide.
  • the title compound was prepared according to General Method A from the compound of Example 63 and 1.3 eq hexachloroethane. Purification by RC using 1:4 ethyl acetate/hexanes gave 500 mg of the title compound as a yellow solid, a 44% yield, m.p. 42-44 °C.
  • Example 70 The title compound was prepared according to General Method A from the compound of Example e and 1.5 eq (chloromethyl) dimethylsilyl chloride. Purification by HPLC using 1:9 ethyl acetate/hexanes gave 5.4 g of the desired compound as a yellow oil, an 85% yield.
  • Example 70
  • the title compound was prepared according to General Method D except that 1-butanol instead of CH 2 Cl 2 was used to extract the boron intermediate.
  • the crude intermediate was further reacted with 2-bromotoluene as described in General Method D to give the title compound as a white solid (recrystallized from toluene) in 55% overall yield, m.p. 131-134 °C.
  • the title compound was prepared from the compound of Example f and 1-bromonaphthalene (0.76 g, 3.65 mmol) according to General Method D. It was obtained as 0.28 g of a white solid, a 28 % yield, m.p. 181-182 °C.
  • the title compound was prepared from the compound of Example 74 and 3.0 eq Mel according to General Method A and recrystallized from cold hexanes/ethyl acetate to give 2.5 g of the title compound, an 82% yield, m.p. 96-97 °C.
  • the title compound was prepared from the compound of Example 45 using the procedure of Example 51. m.p. 158.0-159.0 °C.
  • Example b The compound of Example b (1.48 g, 0.006 mol), CH 2 Cl 2 (50 mL), ethanethiol (0.44 g, 0.007 mol), and 4-(N,N-dimethylamino)pyridine (0.86 g, 0.007 mol) were allowed to stir at RT overnight. The mixture was washed with 10% HCl and three times with water, dried (MgSO 4 ) , and concentrated. The crude product was purified by RC, eluting with 1:3 ethyl acetate/hexanes. The title compound was obtained as a clear oil in 61% yield.
  • N-Ethyl-2-(trifluoromethyl)-6-(trimethylsilyl)-benzamide 2-(Trifluoromethyl)benzoyl chloride and ethyl amine were combined according to General Method E1 and recrystallized from cold hexanes to give 7.7 g N-ethyl- 2-(trifluoromethyl)benzamide as a white solid, a 67% yield, m.p. 73-76 °C.
  • the title compound was prepared from the compound of Example 39 and 1.5 eq hexachloroethane according to General Method A. Purification by RC with 1:4 ethyl acetate/hexanes afforded 320 mg of the desired compound as a white solid, a 14% yield, m.p. 143-147 °C.
  • the title compound was prepared from the compound of Example 39 and 2.0 eq TMSCl according to General Method A. Purification by HPLC with 1:4 ethyl acetate/hexanes gave 0.9 g of the title compound as a white solid, a 37% yield, m.p. 93-96 °C.
  • the title compound was prepared from the compound of Example f and 1.5 eq vinyldimethylsilyl chloride according to General Method C. Purification by HPLC with 1:4 ethyl acetate/hexanes gave 630 mg of the desired product as a white solid, a 9% yield, m.p. 86-89 °C.
  • N,N-Diethyl-2-chloro-3-fluorobenzamide was prepared from N,N-diethyl-3-fluorobenzamide (prepared from 3-fluorobenzoic acid and diethyl amine as generally described above) and 1.4 eq hexachloroethane according to General Method A. Purification by HPLC WITH 1:4 ethyl acetate/hexanes gave 3.3 g of the desired compound as a clear oil, a 56% yield.
  • Example 90 To a solution of the compound of Example f (3.7 g, 20 mmol) and TMEDA (6.0 mL, 40 mmol) in anhydrous THF (100 mL) at -78 °C under nitrogen was added dropwise 1.3M s-BuLi (34 mL, 44 mmol). After 30 min MgBr 2 ⁇ Et 2 O (15.5 g, 60 mmol) was added, and the solution was warmed to ambient temperature, then cooled to -78 °C and stirred for 1 h. t-Butylperoxy benzoate (4.3 g, 22 mmol) was added, and the solution was warmed to -30 °C and worked up in the usual manner. Purification by HPLC with 3:17 ethyl acetate/hexanes gave 1.7 g of the desired compound as a white solid, a yield of 33%. m.p. 126-127 °C.
  • Example 90 To a solution of the compound of Example f
  • Oxalyl chloride (2.2 eq) and the 2,6-disubstituted-benzoic acid (1 eq) from Step 3 were stirred in toluene with catalytic DMF at RT under nitrogen for 1 h. The solvent was removed in vacuo before additional toluene (50 mL) was added and
  • Triethylamine (27.89 mL, 200 mmol) was added to a mixture of the compound of Example b (2.47 g, 10 mmol) and N-propyl-N-iso-propylamine hydrochloride ( ⁇ 92 mmol) in toluene (100 mL). The reaction was stirred overnight at ambient temperature, then was partitioned between ethyl acetate and dilute citric acid. The organic phase was washed with brine, dried (MgSO 4 ), and concentrated to afford 2.50 g of the title compound as a waxy amber solid, an 80% yield.
  • Triethylamine (2.02 g, 20 mmol) was added to a mixture of the compound of Example b (2.47 g, 10 mmol) and N-ethyl-N-(1-methylhept-1-yl) amine (3.15 g, 20 mmol) in toluene (25 mL). The reaction was stirred 2.5 h at ambient temperature, then was partitioned between ethyl acetate and dilute citric acid. The organic phase was washed twice with sat aq NaHCO 3 , followed with brine, then was dried (MgSO 4 ), concentrated, and kugelrohr distilled under vacuum. The fraction which distilled at 157 °C was collected to afford 1.16 g of the title compound as an amber oil, a 38% yield.
  • Example 2 The compound of Example 2 (9.96 g, 40 mmol) and a solution of DMF (3.65 g, 50 mmol) in THF (20 mL) were combined according to General Method A. The resulting reaction mixture was partitioned between ethyl acetate and dilute citric acid. The organic phase was washed with sat aq NaHCO 3 followed with brine, dried (MgSO 4 ), and concentrated to afford 8.35 g of N ,N-diethyl-2-trimethylsilyl-6-formylbenzamide as a white solid, a 75% yield, m.p. 63.5-65.5 °C.
  • Example h To a solution of the compound of Example h (4 mmol) in 50 mL toluene was added 70% ethyl amine (4 mL). The solution was stirred for 0.5 h and then stood overnight. Ethyl acetate was added and the mixture was washed with water. The organic layer was concentrated to a semisolid, which was triturated with hexane. The title compound was collected by filtration as 0.9 g of crystals, an 83% yield, m.p. 161-163 °C.
  • Compound 112 (Z)-2-Chloro-N-1-propenyl-6-(trimethylsilyl)benzamide.
  • Compound 114 A 50:50 mixture of Compounds 112 and 113.
  • Wilkinson's catalyst [tris(triphenylphosphine)rhodium(I)chloride] (80 mg) were dissolved in 100 mL toluene and refluxed for four days. The mixture was filtered through silica gel, which was washed with ethyl acetate and combined with the filtrate. The solvent was removed and the mixture was resolved by RC with 1:9 ethyl acetate/hexane to yield two fractions having different tic spots. The first fraction was concentrated to yield a solid which was recrystallized from hexane to yield 1.9 g of Compound 114 (m ⁇ p. 100.0-105.0).
  • hexamethylditin (5.0 g, 15.3 mmol) was added. The reaction was warmed to -60 °C, and then partitioned between ether and water. The ether was dried (MgSO 4 ), concentrated, and purified by silica gel chromatography, eluting with 1:4 ethyl acetate/hexanes, to afford 4.10 g of the title compound as a white solid, a 77% yield, m.p. 78-80 °C.
  • the title compound was prepared by treatment of 9-bromophenanthrene (0.94 g, 3.65 mmol) according to General Method D. It was obtained as 0.55 g of a white solid, a 56% yield, m.p. 189-191 °C.
  • Example c The compound of Example c (0.0035 mol, 0.95g), 15 mL thionyl chloride, and 1 drop of DMF were combined and stirred at RT overnight. Toluene (50 mL) was added and the mixture concentrated to dryness. This process was repeated three times, and the residue dissolved in CH 2 Cl 2 (50 mL). 2-Methylaniline (0.0035 mol, 0.37g) and triethylamine (0.0035 mol, 0.39g) were added and the mixture was stirred at RT overnight. The mixture was washed with 10% HCl and twice with water; dried (MgSO 4 ) and concentrated. The title compound was recrystallized from hexanes as a tan solid in 71% yield, m.p. 113-115 °C.
  • Example 120 The compound of Example 120 (0.0021 mol, 0.75g) and 50 mL THF were cooled to -78 °C in a nitrogen
  • Example 248 (prepared from diisopropyl amine and 2.5M n-BuLi in hexane according to the method of Example 250) and quenched with TMSCl as in step c of Example 248.
  • the title compound was purified by flash chromatography first with 20%, and then 70% ethyl acetate-hexane as eluent and recovered as a white solid, m.p. 93-95 °C.
  • Example b The compound of Example b (2.47 g, 10 mmol), diisopropyl amine (2.23 g, 22 mmol), and toluene (25 mL) were combined according to General Method E2. The crude product was recrystallized from ethanol/water to afford 1.75 g of the title compound as a white solid, a 58% yield, m.p. 96-97.5 °C.
  • Example 50 The compound of Example 50 (1.33 g, 5.0 mmol) and Mel (2.8 g, 20 mmol) were combined according to General Method B. The resulting reaction was partitioned between ethyl acetate and sat aq NaHCO 3 . The organic phase was washed with brine, dried (MgSO 4 ), and
  • Example b The compound of Example b (4.94 g, 20 mmol), 2-ethoxyethyl amine (3.92 g, 44 mmol), and toluene (35 mL) were combined according to General Method E1. The crude product was recrystallized from aq ethanol to afford 3.97 g of N-(2-ethoxyethyl)-2-chloro-6-(trimethylsilyl)-benzamide as white solid, a 66% yield, m.p. 71-73 °C.
  • Example 127 The compound of Example 127 (0.80 g, 2.9 mmol) was refluxed in a mixture of acetonitrile (20 mL) and 2N HCl (20 mL). Within 2 h the reaction was complete by GLC, and was cooled and partitioned between ether and water. The ether phase was concentrated and purified by RC with 1:4 ethyl acetate/hexanes, then recrystallized from hexanes to give 160 mg of the title compound as a solid, a 21% yield.
  • This compound (1.9 g, 5.1 mmol) and sodium cyanoborohydride (0.32 g) were added to methanol and stirred overnight. The mixture was filtered and water added to the mother liquor. Extraction with ethyl acetate yielded an oil upon solvent removal. The oil was dissolved in 50% ethyl acetate/hexane and filtered through silica gel. Removal of the solvent yielded an oil which was purified by RC (20% ethyl acetate/hexane).
  • Example b 2-chloro-6-trimethylsilylbenzoyl chloride (2.46 g, 10 mmol). After refluxing 4 hrs, allyl amine (0.6 g, 10 mmol) is added and the mixture refluxed overnight. After filtration through silica gel to remove silver salts, the solvent was removed to yield an oil. Trituration with hexane produced 0.7 g of the title compound as a solid, m.p. 68-71 °C.
  • Example 167 The compound of Example 167 (0.47 g, 1.6 mmol) was added to 40 mL 0.5 M sodium acetate solution.
  • Acetone was added to this suspension to a total of 80 mL. Slight warming yielded a homogeneous solution.
  • benzotriazole (1.2 g, 10 mmol) was refluxed 5 days in toluene utilizing a Dean-Stark trap to remove water.
  • This compound was prepared in the first step of Example 164. m.p. 150-151 °C.
  • N-thiomethylphthalimide (5 mmol). After standing overnight, gc/ms suggested close to a 50/50 mix of product to starting benzamide. Water was added and the mixture extracted with ethyl acetate. Removal of the solvent yielded a semisolid. Trituration with 50 mL 15% ethyl acetate/hexane yielded a solid which was filtered off and collected. The mother liquor was purified by RC (20% ethyl acetate/hexane). The first band was collected and stripped to an oil which crystallized upon trituration with hexane and to yield 0.3 g of the title compound, m.p. 92-94 °C.
  • Example d The compound of Example d (38.19 g, 0.13 mol) was reacted with 70% aqueous ethylamine (53 mL) according to General Method E1 and recrystallized from methylcyclohexane to afford the title compound as light tan crystals in 92% yield, m.p. 121-122 °C.
  • Example 179 The title compound was prepared as in Example 179 from isopropyldimethylchlorosilane in 62% yield, m.p. 98°-100° C.
  • Example 185 The title compound was prepared as in Example 179 from phenyldimethylchlorosilane in 44% yield, m.p. 89-91 °C.
  • Example 185 The title compound was prepared as in Example 179 from phenyldimethylchlorosilane in 44% yield, m.p. 89-91 °C.
  • Example 185 The title compound was prepared as in Example 179 from phenyldimethylchlorosilane in 44% yield, m.p. 89-91 °C.
  • Example 185 The title compound was prepared as in Example 179 from phenyldimethylchlorosilane in 44% yield, m.p. 89-91 °C.
  • N-tert butyl anthranilium perchlorate (15.6 g, 56.6 mmol) was added in portions to a solution of triethylamine (17.2 g, 170 mmol) in CH 2 Cl 2 (150 mL). The mixture was stirred at Rt for lh, then was concentrated to a small volume, triturated with ether, and filtered to remove the salts. The filtrate was concentrated and vacuum distilled to give 1.8 g of the N-tert butyl b-lactam as a yellow oil. b.p. 89°-90°C at 0.2 Torr.
  • the 2-chloro-4-bromo-6-trimethylsilylbenzoic acid was diluted with thionyl chloride (3 mL, 41.1 mmol) and warmed. When gas evolution ceased, the solution was concentrated and stripped from toluene (2X) under vacuum to remove the excess thionyl chloride. The remaining dark oil was dissolved in toluene (12 mL), then the compound from example k (2.2 g, 19.5 mmol) was added and the mixture was heated at 100°C until the reaction was complete by GLC.
  • Example 196 The title compound was prepared in an analogous procedure to Example 194, and purified by RC with 1:1 ethyl acetate/hexanes to give a green oil.
  • Example 196 The title compound was prepared in an analogous procedure to Example 194, and purified by RC with 1:1 ethyl acetate/hexanes to give a green oil.
  • Example 196
  • 2,3-Dichloro-6-(trimethylsilyl)benzoic acid was prepared from 2 , 3-dichlorobenzoic acid according to the procedure of example a in 45% yield as 3.07 g of a white solid, m.p. 117-119°C.
  • Example 203 The acid prepared in Example 203 was converted to the acid chloride by the procedure of example b.
  • the acid chloride was reacted with aq O-allylhydroxylamine using General Method E1 to afford the title compound.
  • Purification by recrystallization from ether/hexanes gave 0.68 g of the title compound as a white solid in 86% yield, m.p. 92-94°C.
  • Example 203 The acid prepared in Example 203 was converted to the acid chloride by the procedure of example b.
  • the acid chloride was reacted with 1,1-dimethylhydrazine using General Method E1 to afford the title compound.
  • Purification by recrystallization from ether/hexanes gave 0.62 g of the title compound as off-white crystals in 81% yield, m.p. 144-145°C.
  • Example d The compound of Example d was reacted with propargylamine (3 eq) according to General Method E1 and the crude product was recrystallized from hexanes to afford 0.55 g of the title compound as off-white needles in 81% yield, m.p. 120-121°C.
  • Example 207 The acid chloride prepared in Example 207 was reacted with propargylamine (3 eq) using General Method E1 to afford the title compound. Purification by recrystallization from hexanes gave 0.48 g of the title compound as an off-white solid in 85% yield, m.p. 109-111°C.
  • Example 207 The acid chloride prepared in Example 207 was reacted with cyclopropylamine (3 eq) using General
  • Example 215 The mother liquors from Example 215 were purified by RC (ethyl acetate/hexanes) to give 0.11 g of the title compound in 7% yield as a white solid.
  • the trimethylsilyl ester of 3-chloro-2-fluorobenzoic acid (11.66 g) was prepared in 84% yield using the method described in Example 207.
  • This ester (2.47 g) was converted to 0.45 g of 3-chloro-2-fluoro-6-(trimethylsilyl)benzoic acid in 18% yield using the method of Example 207.
  • the crude product was converted to the acid chloride by the procedure of example b.
  • the acid chloride was reacted with 70% aq ethylamine using General Method E1 to afford the title compound.
  • 2-Phenylbenzoic acid was converted to the acid chloride by the procedure of example b.
  • the acid chloride was reacted with 70% aq ethylamine using
  • This amide (2.25 g, 10 mmol) and TMEDA (1.2 eq) in THF were mixed and cooled to -78°C and a 1.3 M s-BuLi solution in cyclohexane (2.2 eq) was added dropwise.
  • Example 230 The method of Example 230 was followed,
  • Example 222 The compound of Example 222 (0.31 g, 0.85 mmol) was dissolved in CH 2 Cl 2 (20 mL) and was treated with iodotrimethylsilane (2.1 mL, 15 mmol) in a foil-covered flask. The reaction was stirred for 2 h and was
  • Example 222 (0.62 g, 2.2 mmol). The mixture was stirred 45 min, was diluted with water and treated with
  • Example 230 The method of Example 230 was followed,
  • LDA was formed by adding 2.5 M n-BuLi (1.7 mL, 0.004 mol) to diisopropylamine (0.6 mL, 0.004 mol) in 10 mL THF at -78 °C. The mixture was warmed briefly to 0°C then cooled to -78 °C. A solution of the above compound in THF (5 mL) was added. After 0.5 h at -78°C, TMSCl (0.31 mL, 0.0024 mol) was added. The reaction mixture was warmed to -40°C and poured into aq NaHCO 3 and extracted with ether. The ether extract was washed with water and brine, dried (MgSO 4 ) and concentrated.
  • the 2,4-dichloro-N-ethyl benzamide (5.8 g, 0.027 mol) was prepared in 92% yield from 2,4-dichlorobenzoyl chloride (4 ml, 0.03 mol) and ethyl amine (70 wt % in H 2 O) using Method E2.
  • Example 230 The method of Example 230 was followed, substituting 1,2-diiodoethane (2.3 eq) for Mel, to afford the title compound.
  • the crude product was purified by flash chromatography (ethyl acetate/hexanes) and recrystallization from aq methanol to afford 2.72 g of the title compound as white crystals in 71% yield, m.p. 128-130°C.
  • Example 223 To a solution of the compound of Example 223 (0.199 g, 0.7 mmol) in methanol (5 mL) at 0°C was added nitromethane (0.3 mL, 5.0 mmol) and 2.5 N NaOH (2.3 mL, 5.8 mmol) portionwise over 2 h. The suspension was dissolved by addition of ice-cold water and cold 2 N HCl (10 mL) was added. The precipitate was filtered and washed with water to afford the crude title compound. The crude product was purified by recrystallization from aq methanol to afford the title compound as a light yellow fluffy solid (60 mg, 26%). m.p. 104-106°C.
  • Example 239 To a solution of the compound of Example 239 (0.191 g, 0.5 mmol) and palladium tetrakistriphenylphosphine (23 mg, 0.02 mmol) in toluene (10 mL) was added 2 M sodium carbonate (0.5 mL) and phenyl boronic acid (73 mg, 0.6 mmol). The mixture was heated at 90°C for 30 h, additional portions of catalyst (20 mg) and 2 M sodium carbonate (0.5 mL) were added and heating was continued for 24 h. The cool reaction was diluted with CH 2 Cl 2 and washed with 2 M sodium carbonate (50 mL with 5 mL cone NH 4 OH) . The organic layer was dried (MgSO 4 ) and concentrated. The crude product was purified by RC (ethyl acetate/hexanes) and recrystallization from hexanes to afford the title compound as white needles (98 mg, 59%). m.p. 134-135
  • the carboxylic acid was converted to the acid chloride by the procedure of example b.

Abstract

Procédé servant à lutter contre le piétin-échaudage des céréales par l'application à la semence, de préférence, avant la plantation, d'un fongicide représenté par la formule (I), dans laquelle Z1 et Z2 représentent C ou N et font partie d'un cycle aromatique sélectionné à partir de benzène, pyridine, thiophène, furane, pyrrole, pyrazole, thiazole et isothiazole; A est sélectionné à partir de -C(X)-amine, -C(O)-SR3, -NH-C-(X)R4 et -C(=NR3)-XR7; B représente -Wm-Q(R2)3 ou est sélectionné à partir de o-tolyle, 1-naphtyle, 2-naphtyle et 9-phénanthryle, chacun est éventuellement substitué par halogène ou R4; Q représente C, Si, Ge, ou Sn; W représente -C(R3)pH(2-p)-; ou quand Q représente C, W est sélectionné parmi -C(R3)pH(2-p)-, -N(R3)mH(1-m)-, -S(O)p-, et -O-; X représente O ou S; n représente 0, 1, 2 ou 3; m représente 0 ou 1; p représente 0, 1 ou 2.
PCT/US1992/008633 1991-10-18 1992-10-09 Fongicides servant a lutter contre le pietin-echaudage des cereales WO1993007751A1 (fr)

Priority Applications (6)

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SK448-94A SK44894A3 (en) 1991-10-18 1992-10-09 Trisubstituted aromatic compounds, method of their preparation and fungicidal agents
AU28093/92A AU664392B2 (en) 1991-10-18 1992-10-09 Fungicides for the control of take-all disease of plants
HU9401110A HU219131B (hu) 1991-10-18 1992-10-09 Módszer és fungicid készítmény növények torsgombabetegségének gátlására és a hatóanyagok
CA002119155A CA2119155C (fr) 1991-10-18 1992-10-09 Fongicides pour lutter contre le pietin-echaudage des vegetaux
PL92303097A PL170837B1 (pl) 1991-10-18 1992-10-09 S rod ek g r zybobó j c zy PL PL PL PL PL PL
CZ1994887A CZ290470B6 (cs) 1991-10-18 1992-10-09 5 či 6 členné aromáty jako fungicidy pro kontrolu stéblolamu rostlin, způsob kontroly a fungicidní směs k provedení tohoto způsobu

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US78068391A 1991-10-18 1991-10-18
US780,683 1991-10-18
US95199792A 1992-10-02 1992-10-02
US951,997 1992-10-02

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US5486621A (en) * 1994-12-15 1996-01-23 Monsanto Company Fungicides for the control of take-all disease of plants
US6140511A (en) * 1998-06-05 2000-10-31 Monsanto Company Fungicidal compositions and methods of making thereof
US6291513B1 (en) 1998-06-05 2001-09-18 Monsanto Company Fungicidal compositions and methods of making thereof
US9382219B2 (en) 1999-04-15 2016-07-05 Bristol-Myers Squibb Company Cyclic protein tyrosine kinase inhibitors
US8993567B2 (en) 1999-04-15 2015-03-31 Bristol-Myers Squibb Company Cyclic protein tyrosine kinase inhibitors
US7091223B2 (en) 1999-04-15 2006-08-15 Bristol-Myers Squibb Company Cyclic protein tyrosine kinase inhibitors
US6596746B1 (en) 1999-04-15 2003-07-22 Bristol-Myers Squibb Company Cyclic protein tyrosine kinase inhibitors
US7125875B2 (en) 1999-04-15 2006-10-24 Bristol-Myers Squibb Company Cyclic protein tyrosine kinase inhibitors
US7153856B2 (en) 1999-04-15 2006-12-26 Bristol-Myers Squibb Company Cyclic protein tyrosine kinase inhibitors
US7189854B2 (en) 1999-04-15 2007-03-13 Bristol-Myers Squibb Company Cyclic protein tyrosine kinase inhibitors
US6979694B2 (en) 1999-04-15 2005-12-27 Bristol-Myers Squibb Company Cyclic protein tyrosine kinase inhibitors
US8716323B2 (en) 1999-04-15 2014-05-06 Bristol-Myers Squibb Company Cyclic protein tyrosine kinase inhibitors
US7687434B2 (en) 2000-12-22 2010-03-30 Monsanto Technology, Llc Method of improving yield and vigor of plants
US7098170B2 (en) 2000-12-22 2006-08-29 Monsanto Technology Llc Method of improving yield and vigor of plants by treatment with triazole and strobilurin-type fungicides
EP2193711A2 (fr) 2001-09-27 2010-06-09 Monsanto Technology LLC Compositions fongicides et leurs applications en agriculture
US8916555B2 (en) 2012-03-16 2014-12-23 Axikin Pharmaceuticals, Inc. 3,5-diaminopyrazole kinase inhibitors
US9346792B2 (en) 2012-03-16 2016-05-24 Axikin Pharmaceuticals, Inc. 3,5-diaminopyrazole kinase inhibitors
US9365556B2 (en) 2012-03-16 2016-06-14 Axikin Pharmaceuticals, Inc. 3,5-diaminopyrazole kinase inhibitors
US9382237B2 (en) 2012-03-16 2016-07-05 Axikin Pharmaceuticals, Inc. 3,5-diaminopyrazole kinase inhibitors
US9540351B2 (en) 2013-09-18 2017-01-10 Axikin Pharmaceuticals, Inc. Pharmaceutically acceptable salts of 3,5-diaminopyrazole kinase inhibitors
US9546163B2 (en) 2014-12-23 2017-01-17 Axikin Pharmaceuticals, Inc. 3,5-diaminopyrazole kinase inhibitors
US9730914B2 (en) 2014-12-23 2017-08-15 Axikin Pharmaceuticals 3,5-diaminopyrazole kinase inhibitors
JP2019523223A (ja) * 2016-05-30 2019-08-22 シンジェンタ パーティシペーションズ アーゲー 殺微生物チアゾール誘導体
JP7001622B2 (ja) 2016-05-30 2022-01-19 シンジェンタ パーティシペーションズ アーゲー 殺微生物チアゾール誘導体

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CA2119155C (fr) 1999-06-15
US5693667A (en) 1997-12-02
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US5705513A (en) 1998-01-06
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US6133252A (en) 2000-10-17
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HUT66952A (en) 1995-01-30
USRE36562E (en) 2000-02-08
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US6028101A (en) 2000-02-22
US6410558B1 (en) 2002-06-25
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MX184321B (es) 1997-04-04
US5498630A (en) 1996-03-12
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US6252078B1 (en) 2001-06-26
ES2159507T3 (es) 2001-10-16
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US5849723A (en) 1998-12-15
AU664392B2 (en) 1995-11-16
US6248894B1 (en) 2001-06-19
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US6166057A (en) 2000-12-26
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DE69233765D1 (de) 2009-08-27
US5834447A (en) 1998-11-10
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US20010046975A1 (en) 2001-11-29
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LV10020B (en) 1995-02-20

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